Reversible solution pi-dimerization and long multicenter bonding in a stable phenoxyl radical

Chemistry – A European Journal

Chem. Eur. Journal, 24, pp.14906-14910 (2018). (DOI:10.1002/chem.201802204)

Reversible solution p-dimerization is observed in the stable
neutral phenoxyl radical 2,6-bis-(8-quinolylamino)-4-(tertbutyl)
phenoxyl baqp and is spectroscopically characterized. This
behavior, not previously observed for p-extended phenoxyl radicals,
is relevant to the formation of long multicenter bonding in the p-dimer
at low temperature akin to previously reported phenalenyl radicals.
Our experimental data are supported in a quantitative manner by
results from density functional theory (DFT) and ab initio molecular
orbital theory calculations. Our theoretical results indicate that the
solution dimer features strong bonding interactions between the two
phenoxyl rings but that the stability of the dimer is also related to
dispersion interactions between the flanking nearly parallel quinolyl


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